Acetic Acid → HCID 54160474, compound

HRID 1281670Notes

Reaction equation

HRID 1281670 reaction equation
[Br:1][C:2]1[N:6]([C@@H:7]2[O:24][CH2:23][C@@H:18]([O:19]C(=O)C)[C@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)C.C(OCC)(=O)C>O1CCCC1.O>[Br:1][C:2]1[N:6]([C@@H:7]2[O:24][CH2:23][C@@H:18]([OH:19])[C@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 53919136HCID 53919136, compound

Product 1

HCID 54160474HCID 54160474, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-bromo-5,6-dichloro-1-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)-1H-benzimidazole (0.083 g, 0.16 mmol) magnetically stirring in 7 ml of tetrahydrofuran was added sodium carbonate (0.13 g, 1.2 mmol) in 1 ml of water. The mixture was allowed to stir at rt for 7 days, then heated at reflux for 2 h. The mixture was cooled to rt, neutralized with acetic acid (0.059 ml, 1.0 mmol) and stirred for an additional 0.5 h at rt. The product, 2-Bromo-5,6-dichloro-1-beta-D-xylopyranosyl-1H-benzimidazole, was purified on a silica gel column (2.5×10 cm, 230-400 mesh) eluting with ethyl acetate (0.40 g, 0.10 mmol, 63%); m.p. 149.6° C. (decomposes); 1H NMR (DMSO-d6) δ7.95 (s,1H), 7.90-7.80 (bs, 1H), 5.48-5.46 (d, J=5.2 Hz), 5.40-5.30 (bs, 1H), 5.23-5.19 (m, 2H), 3.96-3.90 (m, 1H), 3.85-3.50 (2 overlapping bs, 2H), 3.43-3.20 (m, 2H obscured by HOD peak).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. temperatureThe mixture was cooled to rt
  4. stirringstirred for an additional 0.5 h at rt
  5. customThe product, 2-Bromo-5,6-dichloro-1-beta-D-xylopyranosyl-1H-benzimidazole, was purified on a silica gel column (2.5×10 cm, 230-400 mesh)

Sources & evidence

ORD record
ord-e4442fdd73184ef495d70e343ce02073
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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